Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers

被引：12

作者：

Chen, Dongyin ^{[1
,2
]}

Xu, Chang ^{[1
,2
]}

Deng, Jie ^{[1
,2
]}

Jiang, Chunhuan ^{[1
,2
]}

Wen, Xiaoan ^{[1
,2
]}

Kong, Lingyi ^{[1
,2
]}

Zhang, Ji ^{[3
]}

Sun, Hongbin ^{[1
,2
,3
]}

机构：

[1] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Peoples R China

[2] China Pharmaceut Univ, Ctr Drug Discovery, Nanjing 210009, Peoples R China

[3] China Pharmaceut Univ, Dept Phys Chem, Nanjing 210009, Peoples R China

来源：

TETRAHEDRON | 2014年 / 70卷 / 11期

关键词：

Proton-exchanged montmorillonite; Quinone methides; Benzylation reactions; p-Methoxybenzyl group; Deprotection; SELECTIVE DEPROTECTION; SUBSTITUTION-REACTIONS; CATALYZED BENZYLATION; NATURAL-PRODUCTS; PMB-ETHERS; EFFICIENT; MILD; DERIVATIVES; ALCOHOLS; MECHANISM;

D O I：

10.1016/j.tet.2014.01.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Proton-exchanged montmorillonite (H-mont) was found to be an eco-friendly and cost-effective catalyst for the generation of O-methylated quinone methides (QM) from the corresponding p or o-methoxybenzyl esters and ethers. Nucleophilic trapping of the O-methylated QM with arenes, alcohols, 1,3-dicarbonyl compounds, silyl enol ethers, and allylsilanes has been carried out, respectively, leading to eco-friendly benzylation reactions. Using this protocol, H-mont-mediated deprotection of PMB-protected esters and ethers have been realized for the first time. This work would pave the way for further exploration in O-alkylated QM that are of chemical and biological significance. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1975 / 1983

页数：9

共 67 条

[1]

Alberico D., [No title captured], Patent No. [US 7,928,252 B2, 7928252]

[2] CONCURRENT STEPWISE AND CONCERTED SUBSTITUTION-REACTIONS OF 4-METHOXYBENZYL DERIVATIVES AND THE LIFETIME OF THE 4-METHOXYBENZYL CARBOCATION [J].

AMYES, TL ;

RICHARD, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9507-9512

[3]

[Anonymous], 2006, FOREIGN DIRECT INVES, p[89, 20]

[4]

BALD E, 1979, CHEM SCRIPTA, V13, P47

[5]

Bouzide A, 1997, SYNLETT, P1153

[6]

Boyer S. H., [No title captured], Patent No. [WO 2011038207 A1, 2011038207]

[7] Fe(OTf)3-Catalyzed Reaction of Benzylic Acetates with Organosilicon Compounds [J].

Chan, Li Yan ;

Kim, Sundae ;

Chung, Wan Ting ;

Long, Chong ;

Kim, Sunggak .

SYNLETT, 2011, (03) :415-419

[8] A very practical and selective method for PMB protection of alcohols [J].

Chavan, Subhash P. ;

Harale, Kishor R. .

TETRAHEDRON LETTERS, 2012, 53 (35) :4683-4686

[9]

CONGREVE MS, 1993, SYNLETT, P663

[10] A Practical solution for aqueous reactions of water-insoluble high-melting-point organic substrates [J].

Cui, Xiaoxue ;

Li, Bo ;

Liu, Tianzhen ;

Li, Chunbao .

GREEN CHEMISTRY, 2012, 14 (03) :668-672

← 1 2 3 4 5 6 7 →